Turn Of A Different Century
by VonHosselfratt
Summary: Historical AU. What if Will & Grace was set in 1898 instead of 1998? A series of vignettes exploring these characters in another era. [THIS WAS PUBLISHED IN 2016 SO DON'T @ ME LOL)
1. An End of an Era

**A/N - Not only am I a huge Will & Grace fan, I'm also an avid lover of history so I thought I'd combine the two and explore the question of **_**What if Will & Grace were set a century earlier? **_**It's not supposed to be a hundred percent free of anachronisms - I threw in a few to maintain the feel of the characters - but other than that, it's pretty rooted in the nineteenth century (which is one of my favorite historical eras) I hope you enjoy!**

* * *

 _1898_

William Truman, a refined gentleman and esteemed lawyer, had had a busy morning writing up invoices on his new typewriter, and was taking a well-earned break admiring his freshly-groomed mustache in his hand mirror.

Lost in a reverie of his own handsomeness, he's startled when the door to his office bursts open. Standing there is of his biggest clients, Karen Walker, dressed to the nines in an extravagant feather hat and a flowing, yet well-tailored pinstriped dress.

William would be ashamed to admit, despite his misgivings about the socialite, that her dress alone was enough to take his breath away - albeit not quite in the way that one would expect from a thirty-two year old red-blooded male.

"Mrs Walker," he smiles, standing up and automatically reaching to adjust his tie. "You are, as always, a vision."

"And you look like hell. I thought I told you to do away with the mustache," Karen retorts.

William frowns, then hastily changes the subject.

"It appears you're actually early, for once," he says, pulling his out his pocket watch. "I wasn't expecting you until noon."

"Actually, I'm here about an entirely different matter," the woman says harshly, before stepping into the room, to reveal that she's tugging a struggling young man by the ear.

William furrows his brow.

"Let me take a guess - you discovered another peeping tom outside your chambers?"

Karen lets out a burst of sardonic laughter.

"You're slaying me! This _nancy-boy_ here," she yanks his ear for emphasis, eliciting a pained squeal from the young man, "has been keeping me up day and night with that deranged tone-deaf bird of his, squawking at stupid o'clock in the morning. I can barely hear myself drink!"

"You mean _think_?" Will corrects.

"...Why would I do a thing like that?" Karen says, sounding offended.

"...Never mind."

"If you _must_ know," the man finally speaks, tearing himself free from Karen's grasp, "the _bird_ is called Guapo, and I'm teaching him to sing the National Anthem. We're a double act." He takes a moment to straighten out his suit. "We're going to be performing a duet at Carnegie Hall. We're going to make millions. _Millions, I tell you_!"

"...Jack McFarland, is that you?" Will says, instantly recognizing his old friend. "You're looking well."

"William Truman," Jack says curtly, his icy demeanor concealing his relief at encountering a friendly face. "You've...gained weight."

"It's good to see you too," Will smiles, accustomed to his friend's blunt asides.

Karen watches the exchange, and scoffs.

"Of course, the two nancy-boys know each other. I should have known."

Will stares at them both, and hits an open palm against his head.

"I'm sorry, I forgot to introduce you. Jack, this is Karen Walker, one of my most prized clients. And Karen, this is Jack McFarland, one of my…" he smiles sweetly. "...Dearest friends." He cocks his head. "Albeit one who hasn't contacted me in a long time."

"My _deepest_ apologies," Jack says, "but I've been busy writing my one-man autobiographical play. It's called…" he braced himself. "... _Jack with a J!"_

"...Of course it's with a 'J'" Will replies. "What else could it possibly-"

"It's a working title," Jack snaps.

Karen is eyeing up Jack with renewed interest.

"You're an actor, you say?" she asks, her voice dropping to a drawl.

Jack tilts his head in consideration. "I suppose you _could_ call me a thespian, though I've also dabbled in singing, dancing, composing…"

"...Shoe shining, chimney sweeping, _bathhouse entertaining_ ," Will finishes wryly.

Jack narrows his eyes.

"Well. I gave up on chimney sweeping. It was doing disastrous damage to my hair."

Karen smiles up at the young man.

"So you could say that you're a… _jack of all trades?_ " she says.

"Yes, you could say tha-" Jack's eyed widen, stopping in his tracks. "Ooh, that's what I should call my show. _Jack of All Trades!_ " He jumps up and down excitedly like a young boy.

Will shakes his head, smiling.

"Bully to you, Jack," he congratulates.

Karen trails her eyes down Jack's physique, and strokes her heavily powdered chin.

"Not very lucrative, though, is it?" she comments. "Say, why don't we strike a deal? You get that ghastly bird to shut up, and I will take you on a little excursion to a little place called _Saks Fifth Avenue?"_

"Oh, I've always wanted to go there!" Jack squeals, clapping his hands.

"It literally opened last week." Will says.

"I've always wanted to go there since last week!" Jack corrects, smiling down at Karen. Will rolls his eyes, but smiles at the unlikely friendship unfolding before him.

"You know, I'd also like a trip to the Midtown," he says idly. "I'd love to purchase the new Oscar Wilde book that-"

"You're not invited," Karen cuts in, smiling sweetly.

"Oh."

"Well," she continues, "I'll see you on Friday. For now, I have to get to my new job."

"You, a job?" Will says, surprised.

" _Indeed, a job_ ," Karen spits back. "A girl can't simply spend _all_ day frequenting opium dens and tending to their husband's gout, you know."

"What job, if you don't mind my asking?" Will inquires, taking an idle sip of his coffee.

"If you must know, I'm posing for a new, up-and-coming artist," she says, her eyes flashing. " _Nude."_

Will lurches forward, nearly spitting out his coffee.

Jack gasps. "Posing nude? Why haven't _I_ thought of that?"

"Which artist?" Will says, after composing himself.

"Grace Adler," Karen smiles.

Will's eyes widen in shock.

" _...Grace Adler?_ As in... _my Grace Adler_?"

"That rather depends, is _your_ Grace Adler a Bohemian, bony, red-headed, butch little Gibson Girl Jew?"

"...Yes."

"Huh! Small world, eh boys?" she cackles. "Anyway, I thought it best to immortalize myself in art while I'm still young."

Will bites his lip, resisting the urge to comment.

"Bye, boys," she says, throwing a wink at Jack before disappearing out the door.

Jack stares after her in awe.

"My word, I _love her!_ Say, why haven't you introduced us before?"

"For whatever reason, I didn't predict the sheer chemistry," Will shrugs. He sighs, straightening his suit. "Well, I'm off, too, Jack. I have an important business meeting with a potential client."

"Oh?" Jack says, tilting his head suggestively. "Well, isn't that just a coincidence? I also have a _business meeting_ with a _potential client_ later this evening." He grins impishly. "His name is Javier. He works in construction."

Will fixes him with an incredulous look.

" _No,_ I mean an actual, literal, business deal with an actual potential client!" he says, adjusting his necktie.

"Uh-huh," Jack says, staring at his nails and already losing interest. "Well, you are at least attending my show, correct?"

"...When - or rather, _if_ you get a show," Will chides, glancing over his shoulder. "I will, of course, be in the front row seat."

"Throwing roses at my feet?" Jack says hopefully.

"Perhaps not quite," Will says.

"Oh, trust me, William. When you hear my modern rendition of _Funiculi Funicula_ , you shall be. It may just be the next Lisztomania."

Will shakes his head, but laughs encouragingly and takes another sip of his coffee. "Rather."

"And also, it almost slipped my mind to tell you," Jack says. "I saw Michael yesterday in Coney Island."

Will freezes up, suspending his coffee cup halfway to his mouth.

"He was with a younger fellow," Jack continues airily. "They went on the ferris wheel together."

"The one at Steeplechase?" Will says shakily, and slightly higher pitched. He coughs in attempt to sound unabashed.

"That's the one. He didn't see me, though. I was hiding behind a lady's matinee hat." He laughs. "She accused me of attempting to steal the darn thing. I had to bite my lip to stop myself from telling her, nobody would want to steal it, matinee hats are _quite_ out of fashion."

Will nods, not really listening.

"I have to go," he mumbles, grabbing his overcoat. "As previously stated, I have a … meeting."

He dashes out of the office without another word.

* * *

 **A/N Hope you like it so far! I had to make a few adjustments, i.e Grace's occupation - apparently interior designing didn't exist in the nineteenth century. I'm excited to introduce Grace (among many other characters who will gradually make an appearance. I'll try to include as many characters as possible) Let me know if you want to see a second chapter and I'll work on it right away!**


	2. Confirmed Bachelorhood

"Would you believe," Will says, entering his apartment and hanging his hat, "that Mr. Zamir just stopped me in and hallway and offered me a palm reading in exchange for my _necktie?_ "

Grace Adler, Will's cohabitant and dear friend of many years, sat up in the chaise, an issue of _Vanity Fair_ magazine splayed across her chest.

"And you didn't take the offer?" she replies, nodding towards his tie.

Will scoffs. "Grace, I'm hardly a believer in the occult. That is; if deciphering one's future based on creases in their skin even qualifies as such."

Grace shrugs. "His name is Mr _Zamir_. The name alone gives credence, don't you think?" She stops to preen. " _Apparently_ I'm going to marry a doctor."

"You let him read your palm?" Will says incredulously. "What did you give him in return?"

"Let's simply say he gave me some of _his_ palm." Grace smirks.

"Grace Adler, you harlot."

"It was _over_ the corset, William!

Will shakes his head, before settling down next to her and loosening his tie.

"Oh, Grace. For someone who's lived in New York her whole life, you really have the gullibility of a tourist sometimes."

Grace kicks him sharply. "Ah yes, this is coming from a man who was convinced to buy a Japanese coffee table because the man moving it was cute."

"He was flirting with me!" Will says defensively. "If he hadn't thrown his back out carrying it up here, there would have been a dalliance."

"Well, whilst we're on the subject of things that are _never_ going to happen," Grace murmurs, "My mother called. She still wants to know when we're getting married."

Will pouts in faux-consideration.

"Spring, maybe?"

"Oh, but I'm pining for an autumn wedding," Grace says dramatically, holding a hand to her heart. "And you know how fall colors become me so."

"You would be beautiful in a veil," Will comments, stroking her hair.

"I've already worn one, remember?" Grace scoffs. "When I was...previously betrothed."

"Ah, yes. Daniel," Will says, squinting at the memory in distaste.

"He was an oaf," Grace mutters bluntly. "The sheer amount of baseball games I would have suffered, had I not left him at the altar."

"Please. Between the peanuts and the cracker jacks, you would've been just fine."

"Still. I would rather marry you," she says simply. She rests her head on his shoulder. "Maybe we should just do it. Get married, I mean."

"You and me?" Will says, touched.

"Well, it would certainly fend off my mother from her matchmaking tendencies. Did you know she tried to set me up with a _mortician_?"

"Embalming is a noble profession."

"Yes, but not a sexy one."

"Indeed, I'll give you that."

"...And to think. I have the perfect man, my soulmate, sitting next to me right now. And alas, he's resigned himself to a life of…" she trails off. "Confirmed bachelorhood."

"That's one word for it."

"Why don't we just marry each other, Will?" she says frustratedly, throwing her magazine aside. "Because there is a man out there for you," Will promises, squeezing her hand. "A doctor. Maybe even a Jewish doctor."

"That's a pipe dream right there," Grace grunts. Her mouth twitches. "What about you?"

"What _about_ me?" Will says. "Marriage, for me, is out of the question."

"I know. But between your so-called dalliances, you've yet to settle down. With the exception of Michael, of course…"

Will visibly stiffens. Grace lifts her head from his shoulder, wincing.

"...Did I touch a nerve?"

"No. It's just…" Will sighs. "Jack saw Michael recently. With another man."

"Ah."

"It was the same place Mickey - ahem - _Michael_ and I went on our first excursion. At Coney Island."

"When Harry Houdini was performing?"

"The very same. To think, it's been seven years." Will blinks, his eyes misty. "But; it wasn't meant to be."

"It's okay if you need to cry, Will."

"Cry? Lord, no. I'm just...wistful, I think." He takes a moment to compose himself. "Well, enough skulking around for us. I'm going to take a trolley down to the marketplace, if you'd care to join me?" He stands up and offers his arm, which she takes happily.

"I _do_ need to purchase some oil paint. Mrs Walker has this alabaster skin that is just so hard to capture."

"I'd been meaning to ask you about that," Will says quizzically.

"She's the only model who will work for free. And her notoriety might be beneficial to my career."

"Well, just make sure you make her look good in the painting. I can't afford to lose one of my biggest clients over a misshapen nose or gangly fingers."

"I'm better at fingers, now," Grace snaps curtly.

"Anyway, she seems to have struck up quite the rapport with our Jack. She's taking him to Saks Fifth Avenue, of all places."

"Lucky thing," Grace says bitterly. "Will you take me to Saks?" she adds hopefully.

"Macy's, more like."

She sighs dramatically. "I suppose that will do."

* * *

Karen hums, high-pitched and absentmindedly, as she steps through the doors of her luxurious mansion. She slips off her priceless sable coat and throws it carelessly aside to the doorman. Jack trots in after her, mouth agape.

" _Holy Florence Foster Jenkins_ , this hallway is bigger than my mother's entire house!" he marvels.

"Let me tell you, Jackie, this place seems a lot smaller when you have to share it with two stepchildren and a husband the size of Lucy the Elephant from Atlantic City." Karen says sardonically. "Not to mention my maid who doesn't speak a word of English!"

"I speak English, lady!"

Jack jumps as an aging Hispanic woman appears beside him.

"Don't mind Rosario, she simply...materializes when there's work to be done," Karen says airily, snatching Jack's new tweed overcoat and throwing it in Rosario's direction. "Be a dear and hang this."

Rosario's eyes narrow as she glowers at the socialite.

"Let me explain in terms I think you'll find more coherent... _Hang-o el coat-o_!"

"It's nice to meet you, Rosario," Jack says politely, holding out his hand.

"Oh, darling, you don't need to talk to her. She's just furniture. Like the doorman. Or…" Karen trails off as she sees one of her stepchildren, sitting on the staircase. "...Or Mason. What's Mason doing at home?"  
"He was sent home in disgrace for sneaking into the cafeteria and eating a crater of mutton," Rosario explains bluntly.

"Aw, he's becoming so much like his father," Karen smiles. "Well, Jackie, I was going to meet up with some friends for luncheon anyway. How'd you like to come along?"

"I don't know, Karen. I did tell my mother I'd be at home for luncheon," Jack says hesitantly.

"Lillian Russell's going to be there," Karen coaxes.

"Oh, my days. _The_ Lillian Russell? _I love her!"_ Jack enthuses, instantly grabbing his overcoat back from Rosario. "If only I had my autograph book. Or perhaps a pair of scissors so I can sample a lock of her glorious hair and tape it into my journal."

"You're quite a character. Lillian's going to adore you," Karen grins.

"You know, Karen, I feel this is the start of a glorious friendship," Jack smiles back at her.

Karen links arms with his. "I feel quite the same way, Jackie."

* * *

 **A/N - So glad I got round to updating this! Is anyone else excited about this new Will & Grace revival? Because I am psyched! **


	3. Pimps, Paintings and Poison

1899

"Can you believe Robert and Eleanor are getting married?" Grace enthuses, sighing happily into her coffee cup.

"It's long overdue, if you ask me," Will says idly, putting down his magazine. "They've been courting for what seems like decades ." He frowns at Grace. "You seem happy about this. I thought you hated it when other people found happiness. You seem to spend half your time scowling into wedding announcements in the newspapers."

"Oh, it's different with Rob and Ellen. Something about their relationship makes me feel like I'm not missing out on a great deal." She smiles wickedly to herself. "Besides the fact, I've already sampled the groom. And trust me, dear William, I'm not missing out. Rob wasn't exactly an unforgettable lover."

"Dear Lord, if I could gouge that mental image from my mind, I could," Will complains. "There are some pictures that one doesn't wish to conjure, and one of those things is you and Rob sharing a boudoir."

"Speaking of pictures," Grace smiles, springing up and darting to her easel. "Would you like to see the finished painting of my latest client?"

Without waiting for a response, she picks up her painting and flips it. "Presenting Lord Barry," she says in a sing-song voice.

Will veers back, nearly spilling his coffee. "Wow, you've...really got his cold, dead...piercing eyes pinned down quite adequately," he manages.

"I know. He specifically requested them. I'm sure he's quite eager to hang it in his Great Hall."

"Is that - is that one of those paintings where…" Will begins nervously, feeling a chill run down his spine.

"The pupils follow you no matter where you stand in the room? Yes, and it took me several tries, and by tries I mean days, and by days I mean weeks." Grace takes a mock curtsey. "It drove me quite insane, but the work is finally finished."

"...And how much is he paying you for this? I mean, I'd like to think a man who nearly drove my dearest friend to pupil-related suicide is at least commissioning you a handsome reward…"

"Twelve hundred dollars," Grace says proudly.

"Twelve hundre- Grace! That's more than I make in a year!" Will says incredulously.

"Will, please don't make this about you. That male ego of yours is so unbecoming."

"I mean, I'm happy for you Grace, but-"

"Good! Be happy for me and let's not speak any more of it." She flounces back and sits at the table to eat her cornflakes, shoving her spoon obstinately in her mouth.

"I mean, I'm simply saying, if something is too good to be true, it probably is. There might be a catch. He might...expect something from you."

"He is expecting something from me. A well-proportioned oil painting of his likeness, which I delivered," she gestures to the painting.

"Nothing...untoward?" Will guesses. "When I met him at your office, he seemed rather...off."

"Off?" Grace mumbles, her mouth full of food.

She swallows loudly and glares at Will.

"Yes, Grace, he was...off."

"Off? William, you went to an Ivy League school. Please let your vocabulary reflect that."

"You know... predacious ," Will explains.

"...Okay, maybe dial it down again again just a tad," Grace relents.

"He was creepy, Grace! All...dark, and brooding, and not in a sexy way, like Maurice Barrymore. More like...Big Bad Wolf-type creepy."

"Oooh, and I'm Little Red, and he just wants to eat me up?" Grace mocks. "Is that what you're inferring?"

"Implying," Will corrects.

"Is that what you're implying?"

"Well, if the metaphor fits."

"Well, I promise if I ever deliver any baked goods to my Aunt Honey and find her eyes particularly piercing, I will run for the hills." She snorts at the imagery. "But honestly, Will, I happen to know for a fact that Lord Nathan Barry is not interested in me."

"How do you suppose?"

"Because he's…" she pauses, and begins to shovel cornflakes into her mouth.

Will's eyes narrow. "Grace," he warns.

"You know, these cornflakes are really good," she mumbles. "Quite hard to believe they were invented to alleviate mastubatory practices. I know they're getting me excited."

"You're deflecting. What's your predicament?" Will accuses.

"He'sinterestedinyou," she spits out.

"...What?" Will says, attempting to decipher her food-addled speech. "Why, Grace, I could have sworn you just said-."

"He likes you, Will. He took one look at you and he fell in love." She pauses. "Well. He fell in love with your posterior, at least. He was gazing at it with the most lovelorn look as you were leaving.

"B-but…" Will splutters. "I was only there for a second! To deliver the lucky paintbrush you left behind!"

"Yes, Will! And now he wants... your paintbrush, if you're getting my gist."

"...That's an appalling metaphor! This whole situation is appalling . And now I've lost my appetite." He pauses, looking up at Grace. "And not just because you have cornflakes all over your face."

Grace wipes her cheek with the sleeve of her blouse.

"Oh, Will. He's not so bad as he seems. And he just wants one excursion with you."

"I can't believe you're prostituting me for your own monetary gain!" Will cries.

"And you said I wasn't a shrewd businesswoman," Grace says, quirking a smile.

"You're not a madam! You're a painter! A-a painter with a sudden knack for drawing scary, scary eyes, oh Lord, I can feel them staring at me from across the room…" Will turns to look at the painting, and visibly jerking as he catches sight of the eyes looking at him.

Grace giggles, amused by Will's horror.

"I'm not doing it, Grace. I'm not having a dalliance with a narcissistic, egotistical, condescending monstrosity of a man."

"You know, when you phrase it like that, it appears you and Lord Barry have a lot in common."

"Very amusing, Grace."

"Well, I already agreed that you'd see him, so...looks like you're the Little Red Riding Hood now."

"Grace, please."

Grace gets up and darts behind the painting, putting on a deep, booming voice.

" Will, I just want to love you, and kiss you, " she says, impersonating Nathan Barry. " And if you don't, I'll huff, and I'll puff, and I'll blow your house down."

"That's-that's not even the correct reference," Will rolls his eyes.

"Come on, William," Grace drawls. "Don't you find me...and my vast wealth...at least a little charming?"

"Well, I am in the market for a new pair of buckskin Derby shoes…" Will says, smiling a little.

"I'll buy you all the Derby shoes your heart desires," Grace continues in her booming Nathan Barry voice.

"I suppose all of a sudden your eyes do look rather dashing," Will says, finally playing along.

"All the better to see you with, my dear," Grace continues spookily.

"Okay...okay, stop, stop." Will says, shaking his head. "You're beginning to sound like the ghost of Christmas past."

Grace squeals. "Thank you most kindly," she says, running from behind the painting and planting a kiss on his cheek. "I shall make it up to you. And who knows, perhaps you and Nathan Barry will find true love together.

"And perhaps pigs shall fly, and hell shall freeze over, and Jack shall get find steady employment."

Grace giggles.

"And then perhaps I'll find my Jewish doctor."

"Why does the conversation always circle back to you and Jewish doctors? You certainly won't find one here , holed up in apartment with your nancy-boy best friend."

"You're right. I should go injure myself, on purpose. Or catch yellow fever from one of Jack's Cuban lovers. Maybe then I'll meet a nice Jewish doctor."

"Uh-huh, I'm sure nothing is more irresistible than jaundice, vomiting and bloodshot eyes," Will quips sarcastically.

Grace nods.

"Very well. I'll go get the hammer, and say I stubbed it."

She stands up. "Oh, the things we do for love," she sighs dramatically.

"The things we do for money," Will adds, taking another glance at the painting of his new lover.

"We really are a desperate duo, aren't we, William?" she says.

"Ironically, I think that's also the name of Jack's vaudeville act with his pet parrot."

"Well, we may be miserable, but at least we're not singing with birds."

"Hear, hear," Will agrees. "But, oh, speaking of birds...I wouldn't go out with those feathers in your hair, if I were you. They make you look like Ida Saxton."

"I'm better looking than Ida Saxton!"

"Sure you are, Gracie."

Grace scowls, and tugs the feathers from her hair."You're awfully mean, sometimes."

"Remember, I'm courting the Big Bad Wolf for you," Will reminds her.

"Do you think perhaps that courtship might blossom into something more?" Grace says, perking up a little.

"Not by the hair on my chinny-chin-chin." Will sings back to her.

"...Speaking of the hair on your chinny-chin-chin, you need to visit a barber, you little pig. You're sprouting," she hisses, flouncing from the room.


	4. A Jack of No Trades

An excited knock sounds at the door.

"Come in, Mr Polk," Will says, looking up from his desk.

The door opens and Jack sails into the room, hopping up onto Will's desk before he can object.

"Mr Poke, you say? Who is this, your rough trade lover?" Jack enthuses. "Endearing name, I must say. Does he _poke_ you in all the right places?"

Will sighs, rubbing his temples.

"No. _Harlin_ Polk, my biggest client, is going to be here any minute. And I'd rather you not be here, if it's all the same to you."

"Oh, William, I'm here on official business too. You wouldn't value one client over another, would you?" he pouts.

" _Jack_ , you're not my client. And what _official business_?"

Jack reaches into his coat and pulls out a flier, presenting it proudly to Will.

"It's for my one-man, one-night-only show, _Just Jack_!"

"Just...Jack?" Will is perplexed.

"Yes, but you don't say it like _that._ It's more...oh, we'll go over it later. Anyway, I was wondering if perhaps I could put up a few of these ads outside your-"

"Forget it," Will cuts him off.

Jack frowns. "William, it's just a piece of paper."

"Yes, and this just _my_ firm. I'm not going to tarnish my respectable establishment…"

"Ha! Respectable? This dusty old dungeon? It's underground, Will. Look at the view!" Jack gestures to the window, which featured nothing more than feet walking by.

"It's not so bad," Will says defensively. "On my luncheon break I...sit back, and rate the shoes out of ten."

Jack sighs incredulously. "Why don't we admit what this is _really_ about, William?"

"About...me not wanting your nancy-boy freak show advertised in my office? Because I'll readily admit that." Will turns his back to Jack and picks up the percolator, pouring himself a cup of coffee.

"Well, I was _going_ to say it was about your bitterness of me living the showbusiness lifestyle while you're holed up in this office looking at bad shoes all day, but of course, let's open that other can of worms instead." Jack folds his arms and fixes Will with a stormy glare. "You're embarrassed of me."

" _Jack,_ I…" Will turns around, and pouts at Jack. "Okay, I concede. I'm embarrassed of you. But you have to understand. My client - who brings in ninety percent of my income, might I add - is quite the conservative type."

"Is he from one of... _those_ states? You know, the ones that are shaped like a square?"

"Actually, he's from that rather...big one."

Jack squints.  
"The largest, in fact." Will adds.

Jack cocks his head.

"In the South?" Will offers.

Jack stares at Will blankly.

"The Alamo?"

"William, you're losing me."

"Texas, Jack, he hails from _Texas_. And he's not accustomed to - you know - Northeastern types such as yourself."

"Well, he'd better get used it it! This is New York City, not a run-down saloon in some backwater prairie!" Jack snaps. "You tell him that!"  
"Well, I'm not going to do that," Will says slowly. "Because, you know, I have to eat."

Jack huffs. "I suppose you care more about your job than you do your friends," he says obstinately.

"I do care about you. Enough to tell you that your "showbiz" career, as you put it…" Will rests a sympathetic hand on Jack's shoulder. "...Is not lucrative, not realistic, and simply won't ever happen. You're jeopardizing my real career for your imaginary one. Is that what you want to do?"

"Yes?" Jack says.

Will purses his lips. "Good god, why do I _ever_ try to have a serious moment with you? Go...go ask Karen. I'm sure she can do something for you. Walker Property Management must have a dozen lots in a three mile radius."

Jack sighs. "Karen's done quite enough for me. She's already getting Sarah Bernhardt to attend my performance."

"Dear God! Sarah Bernhardt, I _love_ her!" Will exclaims. "She's coming?"  
"Ha! Of course you wouldn't support a friend, but your ears prick up at the mention of celebrity. Admit it, William, you are just as shallow and hedonistic as…well, _me_!" Jack says.

"Jack, please don't take this personally. This...hobby of yours is endearing. But perhaps you ought to get a real job. Now, I can draw up a resume for you, if I can just get a few references…"

"Oh, I have references," Jack says airily.

"It doesn't count if they're from your mother," Will says.

"What about-"

" _Or_ Rory."

"Well-"

" _Or_ Javier, _or_ Fernando, or any of your foreign construction worker dalliances."

"Oh, but Fernando can vouch for me. He knows I'm a dedicated, hands-on, worker. Can you put that on my resume?"

"...I was thinking more along the lines of retail, not escort work." Will says. "A little place called Bergdorf Goodman just opened in fifth avenue. They're looking for new workers?"

"Oh, Will, their windows are just to die for! Do you think they'd hire me? And do you think they'd let me try on their clothes?"

"Let's put that at number _one_ on the list of things you shouldn't say at the interview."

"You know, you were _much_ more fun in the eighties," Jack muses. "But honest, you think I could make it?"

"Of course. You just need a touch of willpower." Will smiles, adjusting Jack's lapel.

Jack frowns. "What is this _willpower_ of which you speak? If it's your female impersonator name, you need to work on it."

Will laughs, shaking his head.

"Oh Jack. I love you. But please, get out of here before Harlin sees you. But if he does, keep your head down, don't make eye contact, and for the love of god, don't speak. Just pretend you're mute; and that I'm partaking in pro-bono work for the needy."

"See, you're embarrassed of me now. But one day when I'm a star, you'll be telling everyone how you once knew me."

Jack throws his scarf over his shoulder and flounces out.

"I'll see you at my show?" he calls before leaving.

"Front row seats," Will says, amused.

"If you're lucky."

"If _you're_ lucky, rather."

* * *

"Jack, I hope this doesn't sound rash, but...where are we, exactly?" Will says.

Will and Grace glance uneasily around at the seedy surroundings. The bar is mostly empty aside from one passed-out barfly and a rather geriatric-looking bartender.

"Well, it turns out Carnegie Hall isn't quite ready to sample my musical stylings, so for now, this...rustic, yet charming tavern will have to do," Jack explains airily. "You know, all stars have humble beginnings."

"Well, it's very good to see you, Jack," Grace smiles, holding out her hand for Jack to kiss.

"I'm sorry, Grace, but celebrities don't kiss the hands of the commoners," Jack hisses. "You may, however, kiss mine." He juts out his hand.

Grace shakes her head but obliges, bending to kiss his hand.

"You're looking well," she tries.

"I wish I could say the same of you. Is that an Easter bonnet?" he tuts, shaking his head.

"I don't see what's wrong with an Easter bonnet…"

"It's November, Gracie," Will reminds her. "I told you when we were leaving the apartment."

"Bad hair day?" Jack pouts.

"Oh, hush, both of you," Grace scowls. "This is the thanks I get, for coming all the way out here to see you and your god forsaken parrot-"

"Oh, actually it's just me. _Just Jack_ ," he says for emphasis, throwing up his hands and framing his face.

"What's..what on earth is that?" Will says, dumbfounded.

"Oh this?" Jack repeats the gesture. "It just came to me while I was in the tub. It seems to me my greatest genius always seems to strike there."

"Must be a phenomenon that is restricted solely to the bathtub," Will says idly.

"Rude!" Jack hisses, sitting on the piano and swiveling around to face away from them. "When I'm famous, I'll remember who my true friends were."

Will and Grace share an amused look and go to take a seat. Will takes out a handkerchief and gives his chair a quick once-over before sitting down, wrinkling his nose.

"Well, it's not exactly the Royal Albert Hall, but it does get me out of luncheon with Nathan Barry," Will sighs.

"Trouble in paradise, dear William?" Grace mocks.

"Implying there was ever paradise to begin with." Will hits back.

"See, you say that, but I do spy a certain pair of buckskin leather shoes donning your feet." She nods towards his feet, which he is proudly displaying with one leg hooked over the other.

"They do look handsome on me, don't they? But, oh Grace, he is just incorrigible. He's rude to waiters, he's always dropping names - names I don't recognize, might I add - and he constantly cuts me off mid-sentence to inform me that my conversation isn't interesting enough."

"You're lucky, Will," Grace says. "I'd do anything for an assertive suitor. One who buys me things, too, instead of finding "gifts "on the sidewalk and...writing poetry about my eyelashes."

"Trouble in _your_ paradise?" Will notes, raising an eyebrow.

"Oh, Will, you know I care for Joshua. He's the opposite of Daniel in every way, you know."

"Perhaps a little too opposite?"

"There has to be a happy medium _somewhere_ ," Grace laments.

"Oh, I don't know, Grace. I'd say the burden of clairvoyance is much too taxing." Will jokes.

Grace narrows her eyes.

"You do know I hate it when you make jokes like that."

Just then, Karen strides into the room, looking quite out of place in a form-fitting dress and parasol. She's followed by Rosario, who trudges behind her with an indifferent expression on her face.

"Karen! You came!" Jack squeals, jumping up and clapping.

"Anything for my protegee," Karen smiles sweetly, taking a seat beside Will and Grace. She then leans over the whisper to Will through gritted teeth. "Why does this part of town smell like dead birds?"

"Oh, no. That's just Grace's hat," Will whispers back.

Grace nudges him hard.

"Well, it's lovely to see you, Mrs Walker," Will says, slightly louder. "I have to say, I didn't envisage you here. It don't seem to be your preferred venue."

"Well, it was either this, or Olivia's tap dancing recital." Karen sighs. "I suppose the difference here is that I can actually drink during the performance." She produces a canteen and takes a languid swig.

"Welcome to _Just Jack_!" Jack sings. "I'd like to thank you all for being here tonight!"

Will, Grace and Karen glance around for any other audience members.

There is only one woman, who is sat across the aisle in the front tow, beaming up at Jack.

"I love you, Jack McFarland!" she screeches, clutching her pearls.

"Looks as though Jack has got himself a fan." Grace says from the corner of her mouth.

"Wait, that's our neighbor Valerie. We hum together in the elevator," Will notices.

"Huh. Small world."

"Are there any requests from the audience?" Jack says.

Val stands up enthusiastically.

"Can I request you drool in this vial so I can wear it around my neck?" she cries.

"Uh, merchandise is going to cost you. But I like your enthusiasm," he winks.

"I've got a request," comes a monotone voice from the front row. "Don't quit your day job."

"Ah, and if it isn't my lovely wife, Rosario. My next performance goes out to you."

"I will now perform my very own rendition of the classic _Sidewalks of New York_ ," Jack announces, turning to the piano and stretching his fingers dramatically.

"Ugh. Is anyone else tired of this song?" Grace sighs.

"Grace, it's a _classic_. It perfectly sums up life in New York City in the 1890's. It's our theme, our very own Star-Spangled Banner." Will says. " _Aaaand_ Jack's about to ruin it."

" _Down in front of Macy's , perusing the local bazaar, tripping the light fantastic with Rosario Salazar..."_ Jack sings, before hissing, "Love you, Rosie!"

"I always dreamed of being serenaded by my husband," Rosario says monotonously. "I have to admit I'm underwhelmed."

"Is this even legal?" Grace whispers.

"Under parody law, it's quite legal. Unfortunately." Will sighs.

Jack continues his song before finishing, flourishing a hand down the piano and spinning around.

"Well, it's time for a brief intermission. If anyone desires refreshments, the drinks at the bar at on the house."

He giggles.

"And by on the house, I mean courtesy of one William Truman."

Will clenches his jaw. "Damn him! Even at his own show, he's mooching off of me."

"I'll take fourteen gins!" Karen calls. She mutters to Will, "Trust me, I've seen the rehearsals for this show. We're going to need to be highly intoxicated to get through the comedy segment."

* * *

 **A/N - I do want to clarify something about this fic - it's not so much a story as it is a series of historical-themed vignettes inspired by the canon of Will & Grace. It's what I call clumsily chronological - more or less being in order but not totally.**


	5. The Ladies Who Punch

"So, William, what do you think?"

Grace turns to present her visage to her Will, who is perched on the ottoman reading the newspaper. He chuckles to himself.

She clicks her fingers at him, frowning.

"Oh, sorry, dear Gracie. Just reading the funnies. There's this hilarious caricature of Theodore Roosevelt that…"

Grace leans forward and snatches the newspaper from his hands.

"Sorry, sorry. Indeed. Of course. You look handsome, as always, Grace." Will smiles. "Oh. Except...a little more powder, a little less rouge. The waist needs to be tighter and, that hat..." He stands up, squints, and adjusts her hat by a few degrees. "There."

"What about the teeth? Ever since Sarah Bernhardt started using carmine dye on her lips, I've been using it _religiously,_ but I do get paranoid about staining my teeth by accident."

Grace bares her teeth at Will.

He hums, examining her mouth.

"No dye. But you do have a little bit of your breakfast in there."

Grace starts to dig at her teeth with her fingers to remove any offending cornflakes.

"Thank you."

"I wish I could join you at the Spotlight Ball, but I must take the train to Connecticut to see my parents. They keep writing to me to inquire if I've found a wife."

Grace chuckles, as she idly turns and checks herself out in the mirror.

"They still haven't given up on that dream?"

"It seems not. I try to convince them that I'm satisfied with my bachelorhood but they keep insisting that I'm not getting any younger and that-" he stops to do an impression of his mother, "" _The clock is ticking, William!""_

Grace scoffs.

"Oh, hush. For men, that clock does not exist - you can have marriage and children at any point until you're a century old with one wrinkled foot in the grave - but for women, our time comes and goes in a flash. I swear, _my_ mother is so desperate on my behalf it's a wonder she hasn't tried to sell me on the flea market."

Will bites his lip.

"Well - there has been a development in that area. Albeit a tricky one."

"What happened?" Grace turns to stare at her friend.

"I sort of - accidentally, mind - informed my parents that I was...that I had an understanding with someone. A woman, that is." Will shifts uncomfortably, gauging her reaction.

Grace's eye bulge nearly out of her head.

" _What_?"

"Well, mother called the other week, and started going on about the usual charade that Paul had married, and Sam had married - even if the latter is in an utter wasteland of a marriage - and, well, to ward her off, I...invented a woman, so to speak."

Grace sinks down to sit next to Will.

"Go on."

"And, well she insisted on knowing every detail, so I said her name was Anna, and that she was a breathtaking brunette of good social standing with alabaster skin and a beautiful sing-song voice that sounds like bluebirds in the morning."

Grace barks out a laugh.

"That's your fantasy woman, William?"

"Well, I tried to picture what a man would be interested in, in a woman. My mother seemed satisfied. Although now she insists that I bring her to Connecticut to meet the family."

"Oh, Will. What are you to do?"

Will shrugs.

"Maybe I'll say that she died tragically in a trolley accident. Yes, that will do."

Grace shakes her head, laughing.

"That may be your only choice. Where exactly would you manage to find a - a _breathtaking brunette_ with _social standing_ and a _voice like bluebirds_?"

Just then, the door bursts open.

"I need to hide out here," Karen exclaims, closing the door behind her. "That wretched little mole-rat Beverley Leslie is after me."

Will and Grace turn to look at the socialite in confusion.

"I ran into his wife Crystal at Tiffany's the other day. You know, that little old dinosaur who's been slowly croaking since the war of 1812? She had her paws on these diamond earrings which I'd been planning to purchase for myself for the Spotlight Dance. We got into a little fight, and needless to say, the old bat's now in hospital with fragments of porcelain china lodged in her ear."

Will and Grace share a bemused glance.

"Beverley Leslie's been trying to hunt me down ever since. Normally I would just kick him into the sun and be done with it, but if it gets out to the authorities he'll have an opportunity to poach Rosario, and he can't do that because Olivia just started menstruating and there is blood _everywhere,_ Lord, I haven't seen that much carnage since the Civil War, or the last clearance sale at Saks."

Grace slowly turns to Will, raising her eyebrow.

"You know, Karen, you could always hide out in Connecticut."

Will redirects his confusion towards Grace, mouthing, " _What?_ "

"After all, Will _does_ need a lady friend for the weekend." Grace nudges Will.

"Grace, no."

"Well, she would be perfect. She does sound exactly like your Anna."

"Whatever repulsive games you two are planning with me, you can count me out," Karen says harshly, removing her coat. "I'm not privy to the details of your deranged relationship and I don't particularly wish to be."

Grace shakes her head and laughs.

"William needs to escort a pseudo-girlfriend to his parents' house this weekend, and _I_ think you'd be perfect for the role."

Will starts to protest, but catches sight of Karen; amazingly impeccable in white ruffles and lace, her hair perfectly coiffed and braided, diamond earrings glistening proudly, framing her alabaster face.

For such a barbaric drunkard, Karen certainly looked the part.

"...I suppose you'll do," he says slowly. "Your personality would need a tune-up, however."

"I'm not your pygmalion," Karen snaps, moving to unbuckle her heels. "And I'm not your whore. If we're going this, we're going to be doing this my way."

Will purses his lips, deciding not to object. Karen was still his most prized client and he really did need a woman for the weekend.

"Speaking of whores," Karen continues, pausing to give Grace a once-over, "You're wearing a hell of a lot of rouge."

She heads into the bathroom, and Will turns to grimace at Grace.

"It really is a lot."

"The message is quite received." Grace hisses through gritted teeth.

* * *

"So where are we, again? Nantucket?" Karen says airily as they step off the train. Rosario follows behind her, carrying seven of her briefcases.

" _Connecticut_ ," Will corrects her. He nods towards Rosario. "Aren't you going to help her?"

"Uh, I don't _help_ the _help_ ," Karen scoffs, rolling her eyes.

She takes out a pocket mirror and examines herself languidly. "Your folks had better have a lot of alcohol. It's the only way I'm going to get through this wretched charade."

"You needn't worried about that, Karen. My mother has an entire storage room dedicated to her wines."

"...Just one?"

Just then, a ravishing blonde woman steps out onto the platform. She looks icily over the crowd of people and spots Will and Karen. She takes out a handkerchief and begins to wave it.

"Oh, William!" She calls. "Come give your dear mother a kiss."

Will goes to greet his mother with a kiss on the cheek.

"Oh, darling you look so handsome. Much more becoming than your brothers - don't tell them I said that, you know how frightfully jealous they get," Marilyn smiles, stroking Will's face with her hands. "And this must be your lady friend. Uh, Anna, is it?"

"Beaverhausen," Karen pipes up, holding out a limp hand. "Anastasia Beaverhausen."

Marilyn blinks.

"Oh, how delightful. Is that...European?" she says, forcing a bigger smile. "Where are you from?"

"I'm from money, and that's all you need to know," Karen says. "Oh, and Rosario, she's from Mexico."

"I'm from El Salvadore, you drunken gongoozler," Rosario drones.

Marilyn reels back.

"Oh, there's more of you? I only had six chairs for dinner tonight...I suppose I could arrange some furniture…"

"Oh, don't worry about Rosie," Karen says flippantly. "She _is_ furniture."

"Call me that once more, and you'll wake up with furniture down your throat," Rosario hits back.

Will steps in, laughing awkwardly.

"Well, I believe it's time to get back to the house, don't you? I'm sure we're all anxious to - to put our feet up, have a drink…"

"Thank god someone said it," Karen says, shaking her head.


	6. Anna Karen-nina

Will always feels slightly out of place in his Connecticut home - it seemed there was always something left unsaid; from his mother's quiet, cryptic head tilts before she takes a sip of her wine, to his father's furrowed brow as he frequently glances at the telephone between inhales of his pipe.

"So, Anastacia," Marilyn says for perhaps the eighth time that weekend. "Where did you grow up?"  
Will glances anxiously at Karen from across the table.

"Oh, here, there and everywhere," Karen says languidly, smiling to herself. "We had to move an awful lot because my mother was in the circus."

Will almost chokes on his potatoes as she swirls her wine, and chuckles to herself.

"Well. At least, that's the story she tells everyone."

Marilyn opens her mouth, then closes it.  
George glances at his wristwatch, clearly not taking in the conversation.

"Well, how about my William? How did you meet him? I want to know about the exact moment you fell in love with those brown eyes and handsome face…" Marilyn moves to pinch Will on the cheek.

"Mother! I'm thirty-five!" Will protests. "That's enough of the cheek pinching!"

"Oh, Will." Karen sighs. "How could I forget? The first time I laid eyes on him in his...double-breasted Abercrombie and Fitch jacket…"

"Brooks Brothers," Will corrects.

"I was a secretary at his cute little law firm," Karen goes on. "When he first saw me when I walked by his office, he was so entranced by me, he got his tie stuck in the percolator and didn't even noticed until he spilled scalding coffee all over himself!" She stops to cackle at the fake memory.

Will shifts uncomfortably. "Well, I wouldn't say I was _entranced_ …"

"Well, there comes a time when a woman has to say to herself, if a man is willing to make that much of an oaf of himself, she might as well take him to dinner to compensate." Karen goes on. "Oh, and he did _plenty_ of compensating that night." She adds slyly.

"Well, I am just adoring these stories! We must hear more over our nightcap later on." Marilyn smirks, giving Will a satisfied nudge.

Will stiffens, and narrows his eyes a little at Karen who returns it with a playful wink.

"But Anastacia, I have to ask. Are you…" Marilyn falters. "How do I put this delicately, dear? Are you...in possession of a healthy womb?"

Will's eyes widen. He sets down his fork and swallows his steak uncomfortably. "Mother…"

"Darling, I'm simply asking. Are you of a childbearing age?"

"I don't think that's a polite question," Will continues.

Karen turns slightly pale.

"Children aren't really at the forefront of our minds, at the present," Will cuts in again. "I mean…" He stops himself, considering. "Perhaps I'd like to be a father eventually."

"Well, if that's true, there's no time to be wasted? Oh, dear, don't be offended. You seem like a lovely woman; but perhaps not the youngest Will's ever courted. You must be at least a few years older than him, I assume? And you want children yourself?"

Karen remains silent.

Will is dumbfounded - he's never witnessed her in such a subdued state before.

"...I do want a child, perhaps," she says eventually, her voice smaller than usual. "But not with Will."

There's a thick, uncomfortable tension lingering over the dining room. Even George is paying attention as Karen stands up.

"I'm sorry it has to end this way, William. But I'm in love with another man. His name is Stanley Walker and if I ever have a baby, it's going to be his."

She stands up and leaves the room without another word, before quickly running back to retrieve her wine and darting out again.

It's silent once again until the phone rings.

George stands up hastily. "I'll get it. It'll be Tina. I mean...the milkman. Our milkman's name is Tina." He shuffles awkwardly into the kitchen to pick up the telephone.

Will slowly sets down his cutlery and looks at his mother.

"Well. This evening took a rather quick dismal turn." Marilyn sighs, throwing down her napkin. "Who was that woman, again, William?"

Will blinks, and begins to rub his temples.

"Her name is Karen Walker. She's a socialite, and she's married to one of my biggest clients."

"Well. I did think the alias was a bit far-fetched - what was it, _Beaverhausen_?"

Will stands up to begin clearing away the dishes.

"Oh, William, do sit down. The maids will get to it. You and I need to have a talk."

"We never talk about anything," Will says through gritted teeth.

"Well, we never did before, but now we're _both_ adults. I know there are…" she glances out into the kitchen where George's faint murmurs could be heard, "certain things we don't discuss as a family. But when the truth becomes so debilitating, it can burden us in ways we can't imagine."

Will slowly sits down,

"You're a handsome, accomplished man, William. You could have your pick of women. And yet, you seem to never stray from that...unsophisticated, neurotic redhead. I used to believe you had an understanding with her, but…" Marilyn scoffs and trails off, finishing her drink.

Will feels his posture weakening, folding his arms defensively feeling like a child about to be scolded.

"I know you better than you think I do. And if this life you've chosen is one that makes you happy, well…" Marilyn smiles weakly. "There's nothing either of us can do about that."

Will looks up slowly, aghast. "Mother? Are you saying…?"

"I won't say that I'm ecstatic about it. But a mother's job is to love and protect, unconditionally. Now, I'm well aware of the evils in this world. And I know that my son - my favorite son, at that - can't possibly be a part of that."

Will considers outright denying it. But as a weight offers to lift itself from his shoulders, he instead exhales, leaning forward and taking a swig from his drink.

"You know I'm...I'm still a traditional man, Mother. I'm not adverse to the notion of settling down; having children."

Marilyn shakes her head. "No matter how hard you try, William, you will never be traditional. But I do hope you have children, somehow. You always have been my most attractive offspring. Oh, but don't tell Sam or Paul-"

"I won't. Thank you, mother." Will leans forward to kiss his mother on the cheek. He keeps his eyes squeezed shut, knowing it would break his heart to see her flinch.

Marilyn rubs his back tenderly.

"Just for the sake of clarity…" she says. "That man, Jack McFarland, was it? Is he your…"

Will reels backwards, wrinkling his nose.

" _Jack?_ No, mother!"

"Alright, alright, dear, I just had to ask!"

Will gives a forced smile to Fiona, who waddles in to begin clearing away the dishes. As Will moves to help her, Marilyn grabs his hand.

"William…"

"Hmm?"

"I'd hate to see anything happen to you. You'll...be discreet, won't you?"

Will stares at her, then rubs his hand over hers.

"Of course."

* * *

"Grace." Will is breathless as he appears in the doorway, tearing off his coat and immediately moving to pour himself a drink.

"Will, are you quite alright?" Grace wanders into the living area with a mouthful of cookies. She swallows audibly, and whistles. "Two drinks in one day? Connecticut has clearly made its mark on-"

"I want a baby." Will cuts in.

Grace's mouth falls open, crumbs falling out in the process.

"A...a baby?" she echoes.

"Yes," he breathes. "And I want one with you."


	7. Gilded Rage

"Do you think I'd make a good mother, Jackie?" Karen wonders aloud. She's sitting in the bath, turning one alabaster foot idly in the air, examining the crooks of her body. "I haven't told you this before, but...I'm not getting any younger."

"But of course. You're simply amazing with Mason and Olivia. You even learned their middle names," Jack says. He's sitting at the opposite side of the bath, lazily fashioning himself a beard made of bubbles. "And Karen, don't say such things. You're so youthful, like a vampire, or a female Dorian Gray. I'm not entirely unconvinced there's not an old portrait of you up in the attic, withering away like an old hag with...with rotting teeth and weeping boils."

"You're sweet." Karen grins, lifting one idle toe to bop him on the nose. "But…" She sighs, sinking into a more morose stance. "Perhaps I have untapped maternal affection I haven't fully realized. I mean to say, what if I were to have a baby of my own?"

Jack considers thoughtfully.

"What would that be like?" he wonders. "A little baby, with a little high top shoes and little liquor bottles?" He start to giggle at the image. "How ridiculous!"  
"It would be, wouldn't it?" Karen smiles wistfully. "I just don't think Stan would be game for it."

"Hmm, that is a predicament. Well, as a father myself, I can personally vouch for its rewards. There's something so thrilling about knowing that the fruits of your loins are out in the world, swimming freely like little tadpoles."  
"...You're a father?"

"Yes, my son; Elliot."

"Ah, yes. I quite forgot he existed."  
"I often forget, too."

They cackle to themselves, and then sigh.

"Well, I'll always be your baby, Karen." Jackie offers.

"Aw, poodle," Karen smiles. "...How old are you, again?"

"Thirty-four in February," Jack says slowly.

"Uh-huh, so we've got about two or three years before that stops being cute, and starts being sad."

Jack pouts.

* * *

"We have an announcement to make," Grace beams, interlocking her arm with Will's. "We thought we'd throw this little luncheon to commemorate it."

The four are standing in the apartment. Will and Grace are practically humming with excitement, barely able to hold still.

Karen looks down disdainfully.

"Well, it can't be that important an announcement if we're eating on the floor," she says bluntly.

"It's a picnic," Grace says.

"How quaint," Karen says boredly.

"There's a bottle of gin in the basket."

"Well, I suppose I could stay a little while," Karen relents, kneeling to the ground and kicking off her shoes.

Jack folds his arms impatiently.

"Well, it had better be good. I canceled a rather important excursion for this event," he says coldly. "Elliot and I were going to go play baseball in Central Park."

"Oh, we don't want to keep you from that," Will says. "Please, go."

"Please don't make me," Jack immediately begs.

Will purses his lips in amusement.

"It's such a violent game, Will...there's nothing more terrifying to me than balls flying at my gorgeous yet breakable face."

"I'm assuming this is the only context in which you'll denounce them," Grace says, before cackling to herself.

"No-one thinks you're funny, Grace," Jack retorts.

"...Anyway - back to our announcement," Will says, clasping his hands together.

Will and Grace look at each other, grinning.

" _Shall we say it together_?" they say in unison. They throw their heads back and laugh at their synchronicity.

"Oh, Lord, it's finally happened. You two gave in to your crippling loneliness and committed atrocities right here on this floor. Oh, god, I can't believe I'm sitting here," Karen says in disgust.

"Of course not! We're…" Grace grabs Will's hand. "We're having a child."

Jack's mouth falls open, a single grape dropping out rolling to the floor in succession.

"So you _did_ have your wicked way with each other. What did I tell you, Jackie, it was only a matter of time!" Karen scoffs.

Jack rises to his feet, shaking a little.

"How exactly did you achieve this? Might I remind you, William, that you find the female form more revolting than that that wino on 48th street who keeps trying to sell you his toothbrush!"

Jack whips his glare to Grace, pointing an accusatory finger at her.

"It was you, wasn't it?! You're a witch, Grace Adler! Your dalliances with this Spiritualist movement has gone too far! Is it the perfume? It's the perfume, isn't it?" He bends forward to sniff her. "Where can I get some?"

Will shakes his head, and holds up his hands in attempt to assuage Jack's anger.

"Jack, stop."

"Gee, I get one palm reading from Mr Zamir once and now I'm dabbling in the occult? Don't be ridiculous Jack." Grace sighs. "I'm not with child, at _present._ It's a decision Will and I made together. Well, in actuality, it was _his_ idea first."

Jack folds his arms.

"Please tell me this is a joke, William."

"We're serious about this, Jack. Grace and I feel we're at a moment in our lives where we're ready to bring forth a new life. We're excited about it."

Jack physically deflates.

"But-but you already have a child." he says sadly. "Me."

"...Jack?"

"I'm not ready to have a brother," he says sulkily.

"Jack, I'm not your father," Will says incredulously.

"You've been like a father to me. What happens when this child arrives? Will you still love me?"

"Jack, I…" Will stops, before sighing. " _Yes_ , I'll still love you."

"And I'll still be your favorite?"

"...Let's simply say I'll still pay for your bathhouse membership and leave it at that."

"Well, that's good enough for me." Jack says, before leaning over to Grace's belly. "Good evening, little fellow. You're in for a strange life, let me tell you.".

"Jack, I'm not pregnant yet." Grace says bluntly.

There's a loud smash as Karen throws her empty bottle across the room, prompting the other three to stop and turn at her, shocked.

"I'm sick of hearing about this Will and Grace baby nonsense," Karen cries, sounding much like the petulant child Jack had been. She rises effortlessly to her feet, despite her disorientation and extravagant petticoat. "I suppose it's apt that I deliver my own news. I'm going to have a baby, too."

There's silence.

Jack leans forward to grab another grape, pops it into his mouth, then lets his mouth hang open, letting the grape fall out again.

"Karen, I'm...I had no idea," Grace says. "Why didn't you say so? And should you really have drank that whole bottle of gin in…" she leans to grab Will's pocket watch… "two minutes, dear god?"

"I'm not pregnant _yet._ But as soon as this sorry excuse for a party is finished, I'm going straight back to the manse to make love to Stanley. And then I'll have a baby."

The three are dumbfounded.

"Not that I'm not ecstatic for you, Karen," Grace says tentatively. "But...are you sure you're not doing this out of, well, for lack of better word, pettiness?"

"I'm not petty. You're petty," Karen says pettily.

"With all due respect, Karen...having a baby is a big decision. It's not as simple as going out and buying yourself a mink coat, or a ring from Tiffany's," Will explains.

"Oh really?" Karen drawls, shooting daggers at Will, so much so that the man physically recoils, "and what makes you more qualified than me? I mean, look at you!" She gestures at Will and Grace. "How would you feed the baby? You haven't got one good breast between the two of you!"

Grace purses her lips, folding her arms self-consciously over her chest.

"Have you even talked about this with Stanley?" Will presses.

Karen barks out a laugh.

"Don't need to. I'll just go home to the manse, take off my stockings, give Stanley about twenty-eight seconds of afternoon delight, and then button myself up and be on my merry way. He probably won't even be awake for most of it."

"That's the most abhorrent thing I've ever heard!" Will says.

"Oh, and exactly how are you two going to do it?" Karen retorts.

Will and Grace slowly turn to look at one another, with a look of unease.

Will coughs.

"Well, there'll probably be alcohol involved," he says, to which Grace quickly nods in response.

Karen laughs. "Honey, there's _always_ alcohol involved. Doesn't make it any less of a freak show."

"Well, like you said," Grace says quickly. "It won't last long."

Will turns to glare at Grace.

"... _What_?" Grace murmurs.

"I _think_ I can last longer than twenty-eigh- Oh, do forget it, it's ridiculous we're even having this conversation over what was _supposed_ to be a lighthearted luncheon."

Karen moves to put her shoes back on, shaking her head.

"Well, I'm going home to make a baby. Race you to the finish line," she winks at Grace, who screws up her face with disgust.

Just then, a loud, authoritative knock raps at the door.

Jack blinks in fright.

"Oh no, it must be Elliot. He's found me! He already has such gnarly baseball hurling hands...I can already picture him breaking my nose and ruining my career in entertainment."

Will ignores Jack, moving to open the door.

In the doorway stands a police officer with a grave expression.

"...Good afternoon, officer. Can I help you?" Will says

"We were informed Karen Walker was at this address," says the cop. "It's about her husband, Stanley."

"I'm Karen Walker," Karen says. "Is my Stannie okay? Did he drop a chicken leg into an open pothole and then get stuck halfway down the sewers in attempt to retrieve it?" She cackles. "Because it wouldn't be the first time. Or the second."

"Karen, your husband has been taken into custody for tax evasion," says the cop. "We have a warrant to search your home."

"He's...he's been arrested?" Karen gasps.

Jack immediately dives for more grapes.

Karen's lip wobbles a little. "But...we're going to have a baby. I _need_ Stanley." She swiftly adopts an angry stance. "I wish to see my husband!"

"I'm afraid if you want to see your husband, it will have to be during prison visitation hours."

Will turns to look sympathetically at Karen.

Karen nods, sniffing a little. Grace immediately moves to hug her, enveloping the smaller woman in her arms.

Will turns to the cop.

"I'm Mrs. Walker's attorney. Any questions you have for her can be addressed to me."

* * *

Grace has lit several candles, and donned herself in her flowing pink nightgown. The gramophone is playing soft tunes, filling the air with melody. She darts to turn down the lights, to set the perfect atmosphere. _The less visible, the better_ , she thought. _And the more drunk, the better_ , comes the quick afterthought, as she takes a quick sip of wine.

She had thought about throwing rose petals on the bed, but then thought it was perhaps a bit too much - and that her neighbor would not appreciate stealing his prize winning roses from the garden plot.

She waits for Will, perched on the bed, fidgeting nervously.

Why was she so nervous?

It was _Will_ , her dearest friend. If anything, this should feel more natural than with anyone else. Who else would she rather do it with?

 _A Jewish doctor,_ Grace reminds herself.

 _Oh, do shut up!_ Grace snaps at herself. _There is no Jewish doctor. This is as good as it's going to get. Just because one prediction of the future, told to me by my newspaper-stealing neighbor, says I was going to marry a doctor one day, doesn't mean-_

"I'm home," Will calls, slamming the door behind him. Grace quickly composes herself, and rushes to drape herself against the doorway almost mock-flirtatiously.

"Why, hello, there," she purrs.

Will drops his briefcase unceremoniously on the floor, sighing. Grace immediately assumes a more serious stance.

"Are you quite alright, Will?" she says.

"I'm alright, but it's Karen I'm worried about. I stood right by her in the manse while they searched through everything. It was traumatic for her." He begins to pull off his coat, his brow wrinkled with worry. "Oh, and then the reporters started asking me questions, and taking unsolicited photographs of me. Look out for some rather unflattering pictures of me in tomorrow's paper."

"Oh, I'm sure you'll look fine. At least, better than the post-mortem pictures of President McKinley." She giggles.

Will shakes his head.

"Too soon?"

Will moves to pour himself a drink silently.

"Shall we get this deed over with, then?" Will sighs after taking a hasty swig of his drink.

Grace frowns.

"How very romantic," she says sarcastically, imitating a mock swoon. "Casanova has nothing on you."

"I'm sorry," he apologizes. He forces a smile. "You do look lovely," he adds.

Grace returns the smile.

It's silent for a while; only the sound of the gramophone music playing delicately from the bedroom.

"Grace?"

"Yes?"

"Is this Scot Joplin's _The Entertainer?"_ he says incredulously.

"Is was the sexiest song I had," she says.

Will begins to loosen his tie, contemplating.

"Well, I suppose it does add a certain comedy to the situation," he says.

"And it is a _very_ comedic situation," Grace laughs weakly.

She walks backwards into the bedroom, and he follows her nervously.

Grace gulps, but attempts to hide her nervousness with feigned carelessness, turning around the throwing herself languidly onto the bed.

Will watches her, smiling slightly. Unsurprisingly, he is not remotely aroused by Grace's tipsy, kittenish act - an act that would likely send ninety percent of New York City's male population into a state of frenzy - but still feels a rush of affection, watching her kick off her slippers and lie, spread-eagle on the bed with her messy red curls strewn across the pillow.

Indeed, there was no woman he'd rather have mother his child.

And isn't that what matters most?

"I'm ready now," Grace announces.

"I'm not," Will says.

Grace sits up.

"You're wearing far too many clothes," she says.

"I'd rather keep them on, if it's all the same to you," Will says nervously.

Grace cocks her head.

"I think a certain level of undress is required," she says.

"Right. Indeed. Of course. I just…" Will babbles. "It's rather hot in here. Do you mind if I blow out a few of these candles?"

"Be my guest," Grace says.

Will rushes to blow out the candles as he undresses himself, unfastening his suspenders. He attempts to collect himself, breathing methodically through his nostrils and exhaling from his mouth.

Grace waits, feeling rather ridiculous. Lying on a bed, waiting to be inseminated, she feels much like cattle.

She thinks about making a joke about it, but realizes it would probably only worsen the situation.

"Alright. I suppose I'm ready as I'll ever be." Will finally says.

"Oh, good."

"But maybe you could...get under the sheets?"

Grace immediately does so, recognizing that Will's comfort is the most imperative thing. Her own comfort was an afterthought - after all, Will's performance was the most instrumental part of the process; and she had a natural appreciation for the male form.

 _This must be so much harder for him_ , she thinks. _And yet, it's still so hard for me._

Will nervously climbs into bed next to Grace, attempting a disarming smile.

It's ridiculous - they've shared a bed before. They've seen each other in every state of undress before. But this - this was different.

Will's face was still visibly laden with worry and leans towards Grace.

They kiss chastely, a feather-light peck. They remain in this stance, their lips ghosting each others.

Will almost feels like he's kissing a sister. He pulls back slightly.

"Oh, Will," she says, "Are you still thinking about Karen?"

Will laughs. "Believe it or not, Karen isn't exactly the muse of my nighttime fantasies."

Grace shakes her head. "You know what I mean."

"The situation is strife. But she's a strong woman; she'll get through this."

"I can't stop thinking about her; all alone in that mansion," Grace says. "Albeit, with about seventy-five maids, cooks and servants…"

"Hmm."

"...but I think she really needs a real friend right now."

"I'm thinking about Stanley, too," Will murmurs.

"Ah, now is _he_ the muse of your nighttime fantasies?"

" _Grace_!" Will recoils in disgust. "He's in prison! And Karen...she's desperate for a conjugal visit. She says it's because she wants a baby, but deep down I think she's going to miss Stanley."

Grace nods solemnly.

"Well, from this day forth, I'm going to be the best companion she ever had," she says. "Tomorrow, I shall head to the manse and refuse to leave until all of her emotional needs have been met. We'll do everything she enjoys doing - drinking, massages, more drinking, smoking opiates, and of course, spitting at commoners from the balcony."

"You're a simply marvelous friend," Will says. "But I don't believe you know what opiates are."

"I don't care - whatever she pleases, I'll indulge in with her. In time of strife, we often do the most ridiculous things for our friends."

"Like this?" Will says, gesturing to himself and Grace.

"Indeed, like this."

"But perhaps no kissing."

"Kissing is not required."

Will cautiously moves back towards Grace, encircling her in his arms and holding her for a moment.

"We've done this before," he reminds himself out loud.

"We never did cross the finish line."

"Just think of it as a sprint, rather than a marathon."

"The faster we start, the faster it's over."

"Of course."

"And we'll never speak of it again."

"It all makes perfect sense."

"Easy."

"A piece of cake."

"A walk in the park."

"Grace?"

"Yes?"

"I can't do this."

"Nor me."

They exhale in relief and release each other, settling back into their earlier stance. " _The Entertainer_ " is still playing from the gramophone, almost mockingly.

They glance at each other, and then burst out laughing.

They draw back a sigh at the exact same moment.

"Do you still want to have a baby?" Will says.

Grace nods. "Of course I do. I suppose we'll have to...figure something else out."

* * *

Grace hadn't seen it coming.

She was pounding the sidewalks in the most unladylike fashion in haste to get to Karen - whom she had been growing increasingly worried about following her forced separation with Stan - when all of a sudden, she collided into a face-first into a streetlamp.

Though robust by nature, Grace found herself rendered frail in the confines of her corset, and the incident sent her to crumpling the ground immediately, shrieking, at first in shock, then in pain.

As she lay pathetically on her back, her vision slightly blurred and a sharp stinging sensation accumulating above her brow, she thought herself hallucinating when the loud clicks of horse's hooves sounded out against the road; the harrumphs of a horse, and, as she slowly opened her eyes and squinted as the sight above her; the silhouette of a horseman stark against the sunlight.


	8. Dr Leo, I presume

"Good morning, ma'am," says the horseman, tipping his hat. Grace continue to squint up at him as she comes around, watching him dismount his horse and offer his hand.

He's handsome, dressed in a well-tailored reefer jacket and immaculately shined-boots. He has a kind, albeit slightly amused expression, the latter of which sends a wave of annoyance through the woman.

" _Ma'am_ ," she scoffs, taking his hand anyway, "Must you speak to me as if I'm in my fortieth year?"

The man grabs both hands, heaving her to her feet as if she weighed nothing, initiating a flutter in her chest, despite her inner protestations.

"I apologize," the man says sincerely, as she regains her balance and blinks, coming back to reality. "Of course, you don't look a day over twenty-five."

Grace knows he's just flattering, but gives him a reluctant smile.

"Yes, well. I apologize too, that was quite untoward of me. I just became unexpectedly acquainted with this streetlamp, and I'm afraid the pain may have caused me to act rather unbecoming." she replies, stiffly and robotically. "Good day to you, sir."

Still dizzy from the incident (and the encounter with the handsome stranger) Grace begins to stumble away. The man grabs her arm, steadying her.

"Wait, I'm a doctor. I can take a look at that contusion, if you wish. I could prescribe you some medication."

Grace's ears prick up.

"A doctor, you say?" she says slowly.

"Yes, although it would have to be on a non-professional basis. I can't work, it being Yom Kippur and all."

"...Yom Kippur, you say?" Grace whispers, her voice coming out as a hoarse whisper.

She coughs in attempt to recollect herself.

"You're Jewish?"

"Yes. That won't be a problem, will it?"

"No. No, of course not," she replies hastily, trying to convince herself that the last five minutes had been nothing more than a vivid dream. Maybe she had hit her head a little too hard, for a Jewish doctor to horseback ride into her life in such a short space of time would be nothing short of a ridiculous fate, almost mocking of her daydreams.

 _Right now,_ Grace thinks, _I'm probably still lying on the sidewalk, drooling like a bloodhound._

"Perhaps I could give you a ride on my horse? You look a little disoriented," the man says.

Grace blinks then slowly smiles.

Well, if it is just a dream...she may as well enjoy it.

* * *

"Karen, I do apologize for being late," Grace says, rushing into the room. Karen is lounging on the chaise, brushing her wig languidly.

"That's alright, honey. You know, you _just_ missed Alice Roosevelt," she replies, nodding towards the door. "Oh, we had a grand old time. You know, smoking, partying, setting her snake loose and waiting for Rosario to find it in the tub...you know, just girl things."

" _Alice Roosevelt_ was here?" Grace says, starstruck. "Oh, to think I'm standing in the same room as - wait - _Emily Spinach_ is here too?" She shrieks, scrambling onto the nearest couch. "Oh, I'm deathly afraid of snakes. Or anything that slithers, hisses, or…" she winces. "Bites."

"Oh, do relax, Grace, she took Emily Spinach with her. I'm just glad you didn't walk in here five minutes sooner, you would have seen something more distressing." She presses the side of her palm to her mouth and whispers, "We set fire to a voodoo doll of Helen Herron Taft and scattered the ashes out the window onto unsuspecting pedestrians."

"That's just deplorable," Grace says. "If President Roosevelt can't keep his daughter under control, how can I expect him to keep our country under control? I'll think twice before voting for him!" She pauses. "...and by that I mean, I'll think twice before letting Will vote for him."

"Ah, women voting...it's amusing because it'll never happen."

Grace moves to sit on the couch opposite Karen.

"Wait, stop!" Karen yells. Grace freezes, her eyes widening. "Don't sit there. She put a tack on that couch."

Grace leaps up indignantly, angrily choosing to sit next to Karen on the chaise instead. "Must she tack _every_ chair in New York City?" she cries.

"Well, I don't know about _every_ chair, but as of this afternoon, the one in the Oval Office has been covered," Karen shakes her head in amusement. "That Alice is one firecracker, let me tell you that."

"Well," Grace says, adopting a more formal stance. "Besides gallivanting with _eighteen year olds,_ how have you been doing? This separation with Stan must have difficult for you."

"Oh, I'm fine. Don't you worry your pretty little head about me, Grace Adler," she smile wryly. "Let's talk about you."

"Me?" Grace is shocked.

"Oh, honey, I could see it from a mile away. Your cheeks are flushed, your hair's a mess and you have a large bruise forming on your head. You've had a liaison - and not exactly a tender one, at that," she retorts.

Grace's mouth falls open in shock. "I have _not-_ "

"Honey, there's no shame in being a whore. Isn't that what the Suffragette movement is about?" she asks. "But really, Grace I have no idea what it's about. I believe it's something about the right to be fat, or ugly, or just generally repellant to men?"

Grace shakes her head. "Well, I'm certainly not repellant to men. I met one today, actually." She smiles smugly.

"Ha! I knew it!" Karen cries. "You have hysteria written all over your face."

"We did _not_...have relations," Grace says. "he was a...gentleman. I ran into a lamppost, he helped me up, we rode a horse together, and here I am. I never even got his name."

"That's the saddest story I've ever heard," Karen says. "Especially since you're impregnated with nancy-boy sperm."

"I'm _not_ with child!" Grace hisses. She stops, shifting uncomfortably recalling the events of the night before. "Will and I are going to find another way to have a child. Adoption, perhaps."

Karen considers. "Well, just stay away from state orphanages. Those things are chock full of pyromaniacs, drug addicts, boozehounds and psychopaths."

"So...much like you?" Grace hits back.

Karen scoffs. "It's different because I'm rich."

"Ah."

"So, do you think you'll see this man again?"

Grace bites her lip. "I suppose not. It was nice to experience a flirtation, though, despite my commitment to Will."

"Hear hear. Despite my love for Stanley, in this time of oppression and uncertainty, it's always nice to take a walk on the wild side." Karen agrees, reaching for a bottle of champagne. "Let's raise a toast," she says, pouring a glass for her and Grace.

"To Jewish doctors," Grace pipes up.

"To the Roosevelts," Karen adds.

Grace thinks for a moment. "To the suffragettes," she says.

Karen shakes her head. " _Grace_. I'm far too pretty to be a suffragette," she scoffs. "To alcohol?"

"I can't argue with that one," Grace agrees as they clink glasses and drink.

* * *

"You won't believe this, Gracie," Will says, shutting the door and hanging his hat on the coat rack. He presents the newspaper to her. "George Melies has just released an eighteen-minute film, _in color._ " He sighs, pressing the newspaper to his chest wistfully. "The French are so artful, I don't know why I don't just get up and move to Paris myself."

"Eighteen minutes?" Grace says. "I've never heard of a film being so long! I don't think I could ever focus my eyes on a screen for that length of time."

Will loosens his tie, cocking his head. "You'd think so, but it's about time and space travel."

" _Time and space travel_ ," Grace scoffs. "I prefer a good old-fashioned romance."

Will tosses the newspaper to Grace. It hits her lap harshly.

"A Trip to the Moon," he says. "It's set in the future. 2002, if you can believe it."

"2002," Grace repeats. "That doesn't sound like a real year." She picks up the newspaper nonetheless, squinting at the pictures.

"I often wonder what it would be like. Living so far into the future," Will considers. "How different would our lives be?"

"If this is what people are going to be wearing in 2002," she says, "You can count me out of _that_ fantasy."

Will laughs in response, bending to unbuckle his shoes.

"So did you see Karen today?"

"Yes. Would you believe that she is liaising with the first daughter of the United States?" she says.

"Oh, Alice? I _worship_ her." Will gasps. "Did you meet Leo?"

Grace freezes, cogs turning in her mind.

"Leo?" she says.

"Yes. That's the name of her chihuahua - at least according to _Vanity Fair_ magazine…"

Grace remembers now - the name engraved on the gold-plated briefcase the mysterious doctor had been carrying; she vividly recalls the clicks of the case opening as the doctor had produced a bandage and tied to so tenderly to her head. She had never before known how hands could be so cold and so warm at the same time. Her heart shifted in her chest as she remembered... _Leo._

"Grace? Are you quite alright?"

"Yes! Yes, I'm fine. I was just...you know, you got me thinking about baby names." She says hastily.

Will considers as he pour himself a glass of port. "Hmm...how about William Truman the second?" he says.

Grace shakes her head disapprovingly. "Oh, please don't be one of those men who uses having a child as an exercise in narcissism. Besides, a president was _just_ assassinated...the name William is cursed, you know."

"Hmm. Thanks for that," Will says sarcastically.

"I always liked the name Lilly," Grace offers.

"Lilly's a whore's name."

Grace narrows her eyes. "You think every woman's name is a whore's name."

"Theodore?"

"Too topical," Grace dismisses. "And I don't know if I altogether like our president yet."

"You don't like Theodore Roosevelt?" Will says. "I was thinking about voting for him next election."

"Really?"

"Yes; I mean, he's educated, he's brave, he's robust." Will raises a glass to his mouth to take an idle sip.

"Of course, he's robust _now_. But just wait until this afternoon when he gets a tack stuck in his buttocks."

Will pauses, the glass halfway to his mouth, before shaking his head and taking a sip. "I'm not even going to ask."

* * *

 **A/N** **You might have noticed I'm adding some canon to this story (if a little scattered) - that's just to maintain a little structure. This fic was originally going to be a series of vignettes but I'm going to be adding a few elements of canon from now on. Thanks so much for reading!**


	9. A Reluctant Engagement

**A/N: Thank you so much for the reviews! It's been just over a year since I first posted this and I've had so much fun writing it so far. You may have noticed that I eventually started incorporating bits and pieces of canon into the story, albeit very clumsily. That wasn't my intention but I feel like it does give the story a much needed skeleton. Anyway, in this chapter, I steal exactly one (1) joke from the show. This is unprecedented and I'll never do it again lol. thanks for sticking with me thus far!**

* * *

"Happy birthday, Elliot," Jack greets his son outside the penny arcade. The young boy smiles and nods up at his father. "So, how was the arcade? Are you a _hardened gambler_ yet?"

"No, although Nancy and I did use the love tester machine. Apparently we're "hot stuff"," Elliot says to his father.

Jack giggles. "Oh, how I love the modern lingo. So; you and Nancy. Do I hear wedding bells?"

"She almost let me hold her hand once," Elliot smiles dreamily. "So...perhaps?"

Jack squeals. "You know, you are becoming so much like me, young man."

"You're a lady killer too?" Elliot says quizzically.

"Oh, something like that," Jack waves his hand dismissively. "So, let's go get hot dogs and then go shopping for a new ensemble. You're twelve now, you're becoming quite the young gentleman and we can't have you wearing plimsolls anymore."

"Actually, I'm thirteen," Elliot corrects. "And I'm comfortable with what I'm wearing, thanks."

"Oh, Elliot, my dear sweet ingenue. Don't you know, the art of seduction is about beauty over comfort?" Jack tuts, one sympathetic hand on his son's shoulder. "Though I can't blame you for thinking otherwise, you were raised by _quite_ the buxom battleaxe."

"You mean Mother?" says Elliot. "She picked out these plimsolls."

"All the more reason to throw them out. _Now._ Since it's your birthday, I thought I'd go all-out to start you off," Jack presents a gleaming wristwatch from his pocket and presents it to Elliot. "Many happy returns, Elliot."

Elliot gapes.

"Is that...is that a Breguet watch?" he says, taking it tentatively. "Father...this is far too extravagant."

"Yes, and it's worth more that your entire outfit put together, _you're welcome_."

"Gee, thanks." Elliot says.

"One condition though...don't wear it around Will. He's been angling for this kind of watch, and he gets frightfully jealous-"

"You stole it from Will, didn't you?"

"...Little bit."

* * *

At the local coffeehouse, Grace Adler found herself draped languidly, head in one hand, over the table, starting wistfully down at her coffee. She barely hears the squeaking of the chair being pulled out beside her as an other woman places herself opposite Grace and sighs loudly.

"Well, I've had quite the melancholic day," Karen says stiffly.

Grace doesn't respond.

Karen blinks, before sighing again, louder.

Grace continues to stare blankly at her coffee.

"Hey!" Karen snaps, causing Grace to jump, startled, out of her reverie.

"What? Huh?" Grace says.

"Well, that's one way to treat a gal. I've just got back from my conjugal visit with Stanley, and yet your tepid bean water is getting more attention than I am. Focus!" she whines.

"I'm so sorry, Karen. I didn't mean to drift away. I've just been day-dreaming an awful lot lately...I suppose my life has become awfully confusing, and it's just given me a lot to ponder over. You know, ever since I bumped into that mystery man-"

"You're still talking about yourself," Karen says impatiently.

"Good god, you're right." Grace says ashamedly, putting her head in her hands. "I always talk about myself, I don't know why I'm so selfish. You know, I think it's because of my mother-"

Karen rolls her eyes as Grace begins another tangent.

"Stanley's seeing another woman," she cuts in bluntly.

Grace stops in her tracks, her mouth falling open.

"He-what?" she gasps.

Karen nods solemnly.

"But that can't be! He's in a _men's_ prison!"

"Well, the old loon is so fat they had to give him his own luxury holding cell, with its own private caterer. Well, I'm not there to rub lotion on his gout anymore, so that harlot started doing it for him. Now they're in a fully-fledged affair, doing Lord knows what - and I really mean, Lord knows what, because when I first starting courting with Stanley it took me months of excavating alone to navigate through his flab and locate his genitals."

"Oh, Karen. I'm so sorry," Grace says, a hand on her heart. "But it doesn't necessarily mean he doesn't love you. You know, a gentleman does have needs…"

"Yeah? Well, I have needs too!" Karen barks loudly, attracting the attention of numerous coffeehouse patrons who glance in their direction. "Do you know how many times I've been tempted? That handsome, husky plumber at Thanksgiving? That peeping tom outside my chamber with binoculars? The first daughter of the United States? I could have debauched all of these people but I didn't…" her eyes well up with tears. "...out of my love and devotion for Stanley."

Grace reaches across to hold Karen's hand. "Karen, I can only imagine your heartache. If you need anything - anything at all…"

Just then, the door to the coffeehouse opens and in walks a handsome, chiseled man.

"Oh, dear Lord, it's Leo. Quick, go!" Grace hisses, ushering Karen away.

"B-but," Karen says, confused.

"It's Leo," Grace mouths. "Get out!"

Karen stands up, offended, and stalks her ways out, shoving her way past Leo in the process. Leo stumbles slightly, caught off guard by the short angry woman who'd rudely bombarded him.

He sees Grace and quickly cheers up, walking over to her.

"Good afternoon, Grace," he says. "Fancy meeting you here."

Grace turns her head away to hide her smile upon encountering the doctor who'd been haunting her dreams for the past few days.

"May I sit?" Leo presses.

"Well…" Grace says, pretending to consider. "I suppose, if you wish."

She takes an idle, nonchalant sip from her coffee as Leo takes the seat opposite her.

"You know, I must admit...I've been thinking about you a lot these past few days."

"You have?" Grace says, her heart beating faster.

"Of course. The fair, yet rather unladylike redhead, hurtling down the streets unchaperoned, with a brief acquaintanceship with an unforgiving lamppost…quite hard to forget." Leo smiles.

Grace swallows audibly, embarrassed. This was not how she wanted to be remembered.

"How is your head healing up, by the way?" he asks.

"Quite nicely, thank you," Grace says, her face flushing beet red. "But I _can_ be ladylike. I'm ladylike all the time, as a matter of fact. You simply...caught me on a bad day."

"Well, even if that is true - I can't stop thinking about you."

Grace inhales sharply at this revelation, turning to look at the man professing his feelings.

"Forgive me for being untoward, but I feel as though we should get to know each other. I would never forgive myself if I didn't at least try to get to know the woman I've been dreaming of."

Grace blinks, panicking. She had not been adverse to a harmless flirtation, but all of a sudden the alarm bells of potential romance began to sound.

"I...I cant." she chokes out eventually after collecting herself.

"...You can't?"

"I'm sorry, Doctor. You seem a nice man. Perfect, in fact," she says, before squeezing her eyes shut and chastising herself for the latter comment. "But I…"

"Are courting with another man?" Leo says.

"No!" Grace says, a little too quickly. "I'm simply...not in a position to begin a relationship in this phase of my life. I do hope you'll understand." With that, Grace rises from her chair and begins toward the exit.

"Well, we could just talk," Leo says in attempt to stop her.

"No, we must not." Grace hits back defensively. Even talking was dangerous. Grace was well aware of her weaknesses when it came to men. The best option was to quit while she was ahead.

Leo frowns, dejected.

"Well, alright," he relents. "But at least let me prescribe a cream for that contusion of yours." He takes out a piece of paper and scribbles some figures down, before handing it to Grace.

She squints at it. "This is your phone number," she says.

Leo winks in response. Grace stiffens her jaw and turns wordlessly for the exit.

She could not play this dangerous game.

* * *

"I'm thinking of getting a Quadricycle," Will says idly over dinner.

Grace shakes her head as she shoves mouthfuls of potatoes into her mouth. "Absolutely not." she says.

"Why not?" Will says, offended as he cuts up his steak. "You don't think I'd look handsome in a quadricycle?"

"I think you'd look _ridiculous_ in a quadricycle," Grace hits back. "They're already going out of style."

Will harrumphs a little, sulkily stabbing his steak with his fork.

"You know your problem William, is that you're still living in the 90's," Grace continues, shrugging.

"Ha! Says the woman who is still enamored by the invention of the puff sleeve," Will replies snarkily.

Grace narrows her eyes.

"Oh, by the way, I went to Tiffany's today." Will reaches into his pocket and places a small box on the table. "For you," he adds, giving Grace a small smile.

She gasps.

"Jewelry? For _moi_?" she smiles, grabbing the box and tearing it open.

She sees the glisten of a diamond ring and feels her heart stop. She turns pale, and is silent for several seconds.

"Grace?" Will says.

Grace blinks several times, and places the box back on the table.

"Will, what is that?" she says slowly.

"A ring?" Will says, attempting a laugh. "What game are we playing here?"

"Oh." Grace replies.

She turns and rises from her seat stiffly, like a ghost. Will follows her with his eyes.

"Aren't you going to finish your dinner?" he asks.

"I'm not hungry," she says.

"I don't believe I've ever heard you say those words before. What's the matter, Grace?"

"You want us to get married." She says bluntly.

"Well, of course we're getting married. We're having a child, Grace. That is...still the plan, is it not?"

"Yes! Of course. But-but it all seems rather soon." Grace says, her heart pounding in her chest as she begins to pace the apartment.

"Soon? Gracie, you've been angling for this marriage for years! You've always said, 'W _ill why don't we just get married, it would be so easy_!'"

"I know."

"And you did agree to have children with me." Will continues quizzically.

"I know." Grace says, a pained expression on her face. "I just...when I envisaged my engagement, I pictured it slightly more…"

"Romantic?" Will says. "I get get down on one knee, if you so wish…"

"Oh, don't bother," Grace says. "It would make a mockery of our friendship. I just...I need some time, I think."

"Time? For what?" Will says

Grace knows there's no response that could assuage Will. Marriage is the most logical option in this moment, and yet she knows that logic is the last thing on her mind.

After a long stretch of silent, she turns and looks at Will.

"You're right," she says. "Of course, I'm being silly. I will marry you."

Will smiles at her. "I'm glad you came around. Now will you put that wretched ring on? It cost three month's wages and if you don't take the doggone thing out of the box I'd be tempted to wear it myself."

Grace laughs, waltzing back to the table in high spirits and lifting the ring from the box, sliding it onto her finger and holding it up to examine.

"It's beautiful," she smiles. "I love you."

"I love you too."

They grin at each other.

"Our children are going to be so lucky to have us," Will sighs.

"I know, we're quite fabulous."

They settle back into dinner and continue gossiping, with Grace stealing glances at her new ring.

She had indeed silly to be tempted by storybook romance. There was nothing she treasured more than her rapport with Will; and they'd been together for so long. In the end, wasn't that what made for a happy, successful and stable marriage in the first place?


End file.
